511256-75-0Relevant academic research and scientific papers
Synthesis of an F-H gambierol subunit using a C-glycoside-centered strategy
Majumder, Utpal,Cox, Jason M.,Rainier, Jon D.
, p. 913 - 916 (2003)
(Matrix presented) This manuscript describes our synthesis of the F-H subunit of gambierol. In addition to the synthesis of the tricycle, of note is an interesting protecting group influence on the generation of a C(23) C-glycoside as well as the use of r
Total synthesis of gambierol: The generation of the A-C and F-H subunits by using a C-glycoside centered strategy
Majumder, Utpal,Cox, Jason M.,Johnson, Henry W. B.,Rainier, Jon D.
, p. 1736 - 1746 (2008/02/02)
Gambierol, a representative of the marine ladder toxin family, consists of eight ether rings, 18 stereocenters, and two challenging pyranyl rings having methyl groups that are in a 1,3-diaxial orientation to one another. Herein we describe the generation of gambierol's A-C and F-H ring systems and demonstrate the versatility of the glycosyl anhydride, enol ether-olefin RCM strategy to fused polycyclic ethers. This work has both enabled us to generate sufficient quantities of the gambierol precursors and has enabled us to better understand the chemical transformations that were key to these efforts. Fundamental work included efforts to C-glycosides and C-ketosides, Claisen rearrangements, and enol ether-olefin RCM reactions.
